A novel and practical synthetic route for the total synthesis of lycopene

Shen, Runpu; Jiang, Xiaoyue; Ye, Weidong; Song, Xiaohua; Liu, Luo; Lao, Xuejun; Wu, Chunlei

doi:10.1016/j.tet.2011.05.104

Cited by 22 publications

(10 citation statements)

References 10 publications

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“…(E)). The NMR spectral data and FT‐IR transmission value were tabulated and compared with the identified values in the literature to draw the confirmatory conclusion as shown in Table (Johansen and Jensen, ; Shen et al ., ). In addition to these values, few peaks corresponding to carbonyl and hydroxyl groups were also observed in both NMR and FT‐IR, that is, δ 4.04–4.24, 0.7–0.899 and 1097.7, 1159.8, 1745.3 cm −1 , respectively.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic Characterization of Lycopene Extract from Lycopersicum esculentum (Tomato) and Its Evaluation as a Chemopreventive Agent Against Experimental Hepatocarcinogenesis in Mice

Gupta

Bansal

Koul

2012

Phytotherapy Research

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The present study was designed to characterize the lycopene extract (LycT) prepared from tomatoes (Lycopersicum esculentum) and then to evaluate its chemopreventive efficacy in N-diethylnitrosamine (NDEA)-induced experimental hepatocarcinogenesis in female Balb/c mice. The extraction of lycopene was carried out using hexane/acetone/ethanol as an extracting medium and then characterized by ultraviolet-visible, nuclear magnetic resonance and Fourier transform infrared spectroscopy. Chemopreventive efficacy of characterized LycT in vivo was evaluated in terms of hepatic tumour incidence, multiplicity, burden, hepatosomatic index and animal survival rate. Results indicated that average lycopene content of the tomato was 11.6-14 mg/kg tomato weight. Spectroscopic data confirmed the structural characteristics of lycopene in the extract. In the animal study, reduction in tumour incidence (42.05%), tumour burden (1.39) and tumour multiplicity (3.42) was observed upon LycT pretreatment to NDEA-treated animals. Histopathological analysis unravelled that the increased survival rate in LycT + NDEA-treated animals was due to the delay in the formation of aggressive tumour nodules. These observations indicate that lycopene seems to be an able candidate for chemoprevention in hepatocarcinogenesis resulting from NDEA insults.

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Section: Resultsmentioning

confidence: 99%

Spectroscopic Characterization of Lycopene Extract from Lycopersicum esculentum (Tomato) and Its Evaluation as a Chemopreventive Agent Against Experimental Hepatocarcinogenesis in Mice

Gupta

Bansal

Koul

2012

Phytotherapy Research

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“…The Wittig-Horner reaction is adopted as an efficient approach to introduce new double bonds under mild reaction conditions. However, this new route for the total synthesis of all-trans-lycopene iii has a relatively low total yield of 26.9% (Shen et al, 2011).…”

Section: Synthetic Lycopenementioning

confidence: 94%

“…Different chemical synthetic pathways for lycopene have been reviewed (Ernst 2002;Shen et al, 2011), but all cases seem to have disadvantages such as low yields, product instability, low product quality and economically unattractive processes (Naviglio et 15 The chemical synthesis of lycopene from smaller molecules generally involves three steps. In the first phase, a C15 compound is synthesized and then dissolved in methanol.…”

Section: Synthetic Lycopenementioning

confidence: 99%

“…But the reaction conditions for the synthesis of allenic phosphonate from 3-propargylic alcohol and dialkyl chlorophosphite was rigorous and subsequent partial hydrogenation of allenic phosphonate was difficult to finish with high selectivity. Shen et al (2011) has recently reported a practical approach for lycopene synthesis by reacting C15-phophonate 2 and the known C10-triene dialdehyde 3. The key intermediate C15-phophonate 2 could be synthesized in four steps by using 4,4-dimethoxy-3- (Figure 4).…”

Section: Synthetic Lycopenementioning

confidence: 99%

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Natural Origin Lycopene and Its “Green” Downstream Processing

Papaioannou

Liakopoulou-Kyriakides

Karabelas

2015

Critical Reviews in Food Science and Nutrition

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Lycopene is an abundant natural carotenoid pigment with several biological functions (well-known for its antioxidant properties) which is under intensive investigation in recent years. Lycopene chemistry, its natural distribution, bioavailability, biological significance, and toxicological effects are briefly outlined in the first part of this review. The second, major part, deals with various modern downstream processing techniques, which are assessed in order to identify promising approaches for the recovery of lycopene and of similar lipophilic compounds. Natural lycopene is synthesized in plants and by microorganisms, with main representatives of these two categories (for industrial production) tomato and its by-products and the fungus Blakeslea trispora, respectively. Currently, there is a great deal of effort to develop efficient downstream processing for large scale production of natural-origin lycopene, with trends strongly indicating the necessity for "green" and mild extraction conditions. In this review, emphasis is placed on final product safety and ecofriendly processing, which are expected to totally dominate in the field of natural-origin lycopene extraction and purification.

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“…Following deprotection under acidic conditions, aldehyde 198 was condensed with the identical biphosphonic acid 194 to provide the all- E -tetraene 199 . Another Wittig-Horner reaction with diketone 200 provided the all trans -lycopene 201 over five steps in 27% yield (Scheme 36 ) [ 143 ].…”

Section: Isoprenoidsmentioning

confidence: 99%

Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids

Jarchow-Choy¹,

Koppisch²,

Fox³

2014

COC

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Isoprenoids constitute the largest class of natural products with greater than 55,000 identified members. They play essential roles in maintaining proper cellular function leading to maintenance of human health, plant defense mechanisms against predators, and are often exploited for their beneficial properties in the pharmaceutical and nutraceutical industries. Most impressively, all known isoprenoids are derived from one of two C5-precursors, isopentenyl diphosphate (IPP) or dimethylallyl diphosphate (DMAPP). In order to study the enzyme transformations leading to the extensive structural diversity found within this class of compounds there must be access to the substrates. Sometimes, intermediates within a biological pathway can be isolated and used directly to study enzyme/pathway function. However, the primary route to most of the isoprenoid intermediates is through chemical catalysis. As such, this review provides the first exhaustive examination of synthetic routes to isoprenoid and isoprenoid precursors with particular emphasis on the syntheses of intermediates found as part of the 2C-methylerythritol 4-phosphate (MEP) pathway. In addition, representative syntheses are presented for the monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), triterpenes (C30) and tetraterpenes (C40). Finally, in some instances, the synthetic routes to substrate analogs found both within the MEP pathway and downstream isoprenoids are examined.

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A novel and practical synthetic route for the total synthesis of lycopene

Cited by 22 publications

References 10 publications

Spectroscopic Characterization of Lycopene Extract from Lycopersicum esculentum (Tomato) and Its Evaluation as a Chemopreventive Agent Against Experimental Hepatocarcinogenesis in Mice

Spectroscopic Characterization of Lycopene Extract from Lycopersicum esculentum (Tomato) and Its Evaluation as a Chemopreventive Agent Against Experimental Hepatocarcinogenesis in Mice

Natural Origin Lycopene and Its “Green” Downstream Processing

Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids

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